Tobacco smoke filter

ABSTRACT

WHEREIN R11/NR8 represent any one of a polyalkylene group, a fatty acid ester group and hydrogen, at least one of the groups being a polyalkylene group and at least one of the groups also being a fatty acid ester group. The saccharide or saccharide derivative constitutes from 0.01 to 30 percent by weight of the filter.   A tobacco smoke filter is disclosed which is designed to remove some of the harmful and irritating substances from tobacco smoke, the filter comprising a filter-forming material or support which contains ester ether compounds of saccharides. Included are aldohexose and ketohexoses having polyalkylene glycol residues and dissacharides containing said hexoses. The compounds effective for the desired purposes may be represented by the following formulas:

United States Patent Atsushi Saito Toyama-shl;

Fumio Nakayama, Toyama-shi; Bungl 'Iamal, Toyama-shi; Illroj Takahashl,

[ 72] Inventors Hiroshima-ken; Kazuo Kuwahara, Yamaguchi-ken; Takashi Kaneko, Ohtakeshi, all of Japan [21 1 Appl. No. 865,993

[22] Filed Oct. 13, 1969 [45] Patented Nov. 16, 1971 [73] Assignees Mitsubishi Rayon Co., Ltd.; Mitsubishi Acetate Co., Ltd Tokyo, Japan [32] Priority Oct. 19, 1968 [33] Japan [54] TOBACCO SMOKE FILTER 14 Claims, No Drawings Primary Examiner-Melvin D. Rein Attorney-Cushman, Darby & Cushman ABSTRACT: A tobacco smoke filter is disclosed which is designed to remove some of the harmful and irritating substances from tobacco smoke, the filter comprising a filterforming material or support which contains ester ether compounds of saccharides. Included are aldohexose and ketohexoses having polyalkylene glycol residues and dissacharides containing said hexoses. The compounds efiective for the desired purposes may be represented by the following formulas:

CHIORI CHO RgOHC CHORs 5 OR; 0 R4 (1) RIOHC 0 CHIOR5 l CH CORa R:OHCC OR; (11) CHORI i H CUR;

CH ORs and CHgO R1 3111-0 RQOHC (fH ORr wherein R, l [NR represent any one of a polyalkylene group. a fatty acid ester group and hydrogen. at least one of the groups being a polyalkylene group and at least one of the groups also being a fatty acid ester group The saccharide or saccharide derivative constitutes from 001 to 30 percent by weight of the filter.

CHOR1 TOBACCO SMOKE FILTER This invention relates to tobacco smoke filters made of filter forming material containing specific ester ether compounds of saccharides. Tobacco smoke filter of the present invention can remove harmful and irritating substances to human body present in tobacco smoke, thereby making the harsh flavor of tobacco smoke milder to give to smokers satisfactory flavor.

The term "filter-forming material" as employed herein, covers fiber, paper, sponge, felt, granule and powder, from which tobacco smoke filter is produced.

For the production of tobacco smoke filters capable of removing harmful and irritating substances contained in tobacco smoke, there have been used, in general. cellulose, cellulose acetate, starch, starch derivatives, silica gel, activated carbon and polyethylene glycol. These filters, however, are not satisfactory in that they cannot remove harmful substances without decreasing the flavor of tobacco smoke.

it has now been found that the harmful and irritating substances can be removed without decreasing the flavor by using filter-forming material containing specific ester ether compounds of saccharides.

The ester ether compounds of saccharides of the present invention are those of hexoses such as aldohexoses and ketohexoses having polyalkylene glycol residues and those of dissacharides containing said hexoses. When classified into pyranose-type and furanose-type compounds, the above-mentioned ester ether compounds may be represented, respective ly, by the general formulas shown below.

CH/ com (II) CHzOR;

III H CORi on o CHgORu and cH-o ctr-'0 mono on no cH-cfi -o CH,ORa

CHORr CHC (5R R0 ln the above general fonnulas (I), (II), (III) and (IV), R,, R R R R,, R,,, R and R represent one member selected from the group consisting a monovalent organic residue and hydrogen atom, one of said organic residue being a polyalkylene glycol ether group of the formula alkylene-(-O alkylene-),,-OH, e.g. a polyethylene glycol ether group of the formula -C,H (OC,H.--),,-OH; at least one of the remaining said organic residue being an acyl group of the formula RCO, e.g. an acyl group having two to l9 carbon atoms.

This is, the present invention is concerned with a tobacco smoke filter made of filter-forming material containing at least one of the compounds represented by the general formulas (I), (ll), (Ill) and (IV).

Each of the above-mentioned compounds has nonionic surface activity and is excellent in ability of absorbing such irritating components contained in tobacco smoke as phenols. When a tobacco smoke filter made of filter-forming material containing such compounds is used, undesirable components present in tobacco smoke, e.g. phenols, can be removed without decreasing the flavor of tobacco smoke.

The aldohexoses belonging to group (I) include glucose, galactose, mannose, etc., the ketohexoses belonging to group (ll) include fructose, sorbose, etc., the disaccharides belonging to group (III) include sucrose, etc., and the disaccharides belonging to group (IV) include lactose, cellobiose, maltose, etc.

The acyl groups to be added to said saccharides include fatty acid ester groups of fatty acids having two to 19 carbon atoms, such as acetyl, propionyl, stearyl, palmityl, oleyl, lauryl and myristyl groups. The number of carbon atoms of said fatty acids is preferably within the above-mentioned range from the point of ability of the resulting compounds for removing undesirable components present in tobacco smoke and melting point and viscosity of the resulting compound.

Further, the polyalkylene glycol residues to be added to the aforesaid saccharides include polyethylene glycol, polypropylene glycol, polyethylenepropylene glycol and polybutylene glycol residues. The chain length of said polyalkylene glycol residue greatly affects the resulting compounds in surface active characteristics, viscosity, and melting point. And the chain length of the polyalkylene glycol residue is preferably in such a range that l to 50 moles, more preferably 5 to 20 moles, of alkylene glycol monomer has been condensed, from the point of ability for removing the harmful and irritating components, precessability of the filter-forming material and the dimensional stability of tobacco smoke filters to be obtained.

Thus, the compounds to be contained into the filter forming material in accordance with the present invention are, for ex ample, as follows:

The compounds belonging to group (I) are glucose acetate polyethylene glycol ether, galactose acetate polyethylene glycol ether, mannose acetate polyethylene glycol ether, etc., the compounds belonging to group (ll) are fructose stearate polyethylene glycol ether, sorbitose stearate polyethylene glycol ether; etc.; the compounds belonging to group (Ill) are sucrose palmitate polypropylene glycol ether; and the compounds belonging to group (IV) are lactose palmitate polypropylene glycol ether, etc.

In accordance with the present invention, filter-forming material containing one or two or more of the compounds belonging to the above-mentioned group is shaped into tobacco smoke filters.

The filter-forming material employed for preparing the tobacco smoke filter in the present invention includes viscose rayon, cellulose acetate, polyarnide, polyolefin or polyester fiber, paper and polyvinyl alcohol, cellulose acetate, polystyrene sponge. The fiber has preferably a single fiber denier of l to 10 and a total denier of 20,000 to 100,000. The fibers may be crimped. The filter-fanning material may also be granules or felt.

The above-mentioned compound is added to the filterforrning material by the following manner: In case of the filter-fonning material is fiber, a solution or dispersion containing the compound is added to the fiber as an oil agent at extrusion step. Alternatively, a solution or dispersion containing the compound may be sprayed to the fibers in a plug machine where the fibers are rolled up to a rod-shaped filter plug. In this case, plasticizers and adhesives may be simultaneously added to the fibers.

In case the filter forming material is in other form than fiber, the compound is mixed with, penetrated into, or adhered onto the surface of, said filter-forming material. In spraying a dispersion containing the compound onto the filter forming material, it is markedly effective for the uniform adhesion of the compound onto the filter-forming material to use other surface active agent such as sucrose ester, polyalkylene glycol or the like as stabilizer of dispersion.

In any of the above-mentioned cases, the content of the present compound in the filter-forming material is 0.01 to 30 percent, preferably 0.05 to 20 percent by weight. If the content is less than 0.01 percent, the effect of the present invention is difficulty displayed, while if the content is higher than 30 percent, the filter to be obtained is not satisfactory in such dimensional stability required for tobacco smoke filter as hardness and in pressure drop characteristics.

In the present invention, substances capable of enhancing the filter characteristics, such as plasticizers, adhesives, and flavors, etc. may be simultaneously added with the present compound to the filter forming material.

The present invention is illustrated below with reference to examples.

EXAMPLE 1 An acetate fiber tow having 18 crimps per 25 mm., a single fiber denier of 4 and a total denier of 55,000 was thoroughly opened. Thereafter, a 10 percent aqueous emulsion of sucrose monopalmitate polyethylene glycol ether (condensate containing 10 moles of ethylene glycol) was uniformly added to the tow by use of a centrifugal spraying means so that the amount of said sucrose monopalmitate polyethylene glycol ether became 1 percent based on the weight of the tow. Subsequently, the tow was rolled up with paper, using a filterplug-making machine, to a rod of 7.9 mm. in diameter and was then cut to a filter plug of 102 mm. in length. The thus-shaped filter plug was cut to filter tips of 17 mm. in length. These filter tips were individually attached by scotch tape to one end of cigarettes to prepare samples for measuring the pressure drop and the amount of phenols in tobacco smoke and for organoleptic test.

n the other hand, a control filter was prepared under the same conditions as above, except that the percent aqueous emulsion of sucrose monopalmitate polyethylene glycol ether was not added.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filter to obtain the results as set forth in table I. 4

The tobacco smoke filter of the present example was excellent in ability of removing phenols in tobacco smoke and, according to organoleptic test, flavor of tobacco smoke passed through the filter of the present example was rich taste and good mildness.

TABLE 1 Phenols Pressure in smoke dro (mgJclg- Kind of filter (mm. H20; arette) Control filter 0. 046

I liter of Example 1 Smoking interval: 30 seconds Smoking time: 2 seconds Amount of flow: l7.5 ml./sec. Length of stub: 30 mm.

Column:

Dioctyl sebacate l0% Phosphoric acid 2% Diasolid-S 3 m., 60-80 mesh (Diatomacenus earth) Temperature:

Thermostat I30 C. Inlet 200' C. Detector I00 C. Detector:

Hydrogen flame ion. Carrier gas:

N, l0 ml.l4.2 sec. H. l0ml./l3.5 sec. Air 10 ml./l .4 sec. Organoleptic test method:

The flavor of tobacco smoke was tested by 20 panel members with respect to the 4 items of aroma, taste, odor, mildness, and there were described items in which significant differences had been recognized.

Example 2 In the same manner as in example 1, except that the aqueous emulsion containing organoleptic 10 percent of sucrose monostearate polyethylene glycol ether (condensate containing 10 moles of polyethylene glycol) and 3 percent of sucrose dipalmitate was employed.

On the other hand, a control filter was prepared under the same conditions as above, except that the aqueous emulsion containing 10 percent of sucrose monostearate polyethylene glycol ether and 3 percent of sucrose palmitate was not added.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filters to obtain the results as set forth in table 2.

The tobacco smoke filter of the present example was excellent in ability of removing phenols in tobacco smoke and, according to organoleptic test, the flavor of tobacco smoke passed through the filter of the present example was extremely rich in taste and good mildness.

EXAMPLE 3 After spinning, an acetate fiber tow having a single fiber denier of 4 and a total denier of 55,000 was treated with an emulsion oil agent comprising 12 parts of mineral oil, 8 parts of sucrose dipalmitate polypropylene glycol ether (condensate containing 8 moles of propylene glycol) and parts of water, so that 2 percent based on the weight of the tow of the emulsion oil agent was adhered to the tow. After treatment with the emulsion oil agent, the tow was subjected to crimping to develop l8 crimps per 25 mm. and was then dried.

This acetate fiber tow was thoroughly opened, was contained 6 percent on the weight of the tow of triacetin as a plasticizer, was rolled up with paper, using a filter-plug-making machine, to a rod of 7.9 mm. in diameter and was then cut to a filter plug of I02 mm. in length. The thus-shaped filter plug was. cut to filter tips of 17 mm. in length. Subsequently, the filter tips were individually attached by Scotch tape to one end of cigarettes to prepare samples for measuring the amount of phenols in tobacco smoke and for organoleptic test.

0n the other hand, a control filter was prepared under the same conditions as above, except that a commercially available oil agent for acetate fiber tow was used in place of the emulsion oil agent.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filters to obtain the results as set forth in table 3.

The tobacco smoke filter of the present example was excellent in ability of removing phenols in tobacco smoke and, according to organoleptic test, the flavor of tobacco smoke passed through the present filters was extremely in rich taste and good mildness.

TABLE 3 Phenols Pressure in smoke dro (mg/cl Kind of filter (mm. H20 arette Control filter 48 0. 036 Filter 01 Example 3 48 0. 032

EXAMPLE 4 A mechanically crimped polypropylene fiber tow having a single fiber denier of 9.5 and a total denier of 60,000 was thoroughly untwisted. Thereafter, a 10 percent aqueous emulsion of glucose diacetate polyethylene glycol ether (condensate containing 10 moles of ethylene glycol) was uniformly added to the tow so that 1 percent based on the weight of the tow of the glucose diacetate polyethylene glycol ether was added to the tow. Subsequently, the tow was rolled up with paper, using a filter-plug-making machine, to a rod of 7.9 mm. in diameter and was then cut to a filter plug of 102 mm. in length. The thus shaped filter plug was cut to filter tips of 17 mm. in length. These filter tips were individually attached by Scotch tape to one end of cigarettes to prepare samples for measuring the amount of phenols in tobacco smoke and for organoleptic test.

On the other hand, a control filter was prepared under the same conditions as above, except that the 10 percent aqueous emulsion of glucose diacetate polyethylene glycol ether was not added.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filters to obtain the results as set forth in table 4.

The tobacco smoke filter of the present example was excellent in ability of removing phenols in tobacco smoke and, according to organoleptic test, the flavor of tobacco smoke passed through the filter of the present example was in rich taste and good mildness.

EXAMPLE 5 A cellulose powder of about 0.8 mm. in grain size was immersed in an aqueous emulsion containing a mixture of 5 percent of glucose diacetate polyethylene glycol ether (condensate containing 10 moles of ethylene glycol) and 5 percent of fructose monooleate polyethylene glycol ether (condensate containing 5 moles of ethylene glycol), so that 4 percent based on the dry weight of the powder of the mixture of ester ether compounds of saccharides was adhered to the powder. Afier drying, 0.4 g. of the thus-treated cellulose powder was packed into a plastic cell of 9 mm. in diameter and 35 mm. in length, and the cell was inserted in a cigarette pipe to prepare a sample.

0n the other hand, a control was prepared in the same manner as above, except that the cellulose powder was not immersed in the aqueous containing the mixture of ester ether compounds of saccharides.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filters to obtain the results as set forth in table 5.

The filter of the present example was excellent in ability of removing phenols in tobacco smoke and was in rich taste and good mildness.

The methods for measuring the pressure drop and the amount of phenols in tobacco smoke, and the organoleptic test in the present example were effected by smoking four cigarettes with one cell.

TABLE 5 Phenols in smoke (mg/cigarette) Kind 0! filter Control filter Filter of Example 5 EXAMPLE 6 Example 1 was repeated except that viscose rayon staples having 10 crimps per 25 mm., a single fiber denier of 4, apparent silver denier of 50,000 and cut length of 51 mm. were employed.

On the other hand, a control filter was prepared in the same manner as the present example except that the 10 percent aqueous emulsion of sucrose monopalmitate polyethylene glycol ether was not added.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filter to obtain the results as set forth in table 6.

TABLE 6 Phenols in smoke e/ sarette) dro (mm. H30

Kind of fllter Control filter Filter of Example 6 According to organoleptic test, the flavor of tobacco smoke passed through the filter of the present example was rather harsh taste.

EXAMPLE 7 TABLE 7 Phenols Pressure in smoke dro (mg/cig- Klnd of filter (sponge) Dipping (mm. H arette) PolyvlnylaleohoL. .NJQQI... 32 0.062 Yes. 32 0.059

Cellulose acetate. No 0.051 Yes. 33 0. 046

Polystyrene. No. 37 0.071 Yes. 37 0.067

Polyvinyl acetate No.. 33 0.057 Yes. 33 0. 053

EXAMPLE 8 Cellulose paper of 10 g./m. was unifonnly sprayed with an aqueous emulsion containing 10 percent of sucrose monopalmitate polyethylene glycol ether. Weight increase of the paper was 1 percent. The paper was cut into I02 mm. length and 25 mm. width, and five sheets of the cut papers were piled and rolled up to make a filter plug of 7.9 mm. in length, attached by Scotch tape to one end of cigarettes to prepare samples for measuring the pressure drop and the amount of phenols in tobacco smoke and for organoleptic test.

On the other hand, a control filter was prepared under the same conditions as above, except that the aqueous emulsion was not sprayed to the paper.

The filter of the present example and the control filter were compared in pressure drop and in amount of phenols in tobacco smoke passed through the filter to obtain the results as set forth in table 8.

As is clear from the above examples, a tobacco smoke filter made of the filter-forming material containing the ester ether compounds of saccharides is excellent in ability for removing the harmful substances present in tobacco smoke due to the nonionic surface activities of the compounds. And the compounds are easily penetrated to the filter-forming material.

What is claimed is:

l. A tobacco smoke filter conforming to the smoke passageway of a tobacco smoking article, said filter comprising a filter-forming material containing 0.01 to 30 percent by weight of at least one member selected from the group consisting ofcompounds represented by the general formulas moms omen,

R OHC-CHOR;

([JH OR; H10 0 Rs CH-C l OR. R1 (Ill) and 011,03 CHO Rt CH-O (in, OR OR: 0R0

wherein R R R,, R,, R R R, and R represent one member selected from the group consisting of l) a polyalkylene glycol ether group selected from the group consisting of polyethylene glycol ether group, polypropylene glycol ether group, polyethylenepropylene glycol ether group and polybutylene glycol ether group (2) a fatty acid ester group and (3) hydrogen, one of R, to R, being said polyalkylene glycol ether group and at least one of the remainder of R to R, being a fatty acid ester group.

2. A tobacco smoke filter according to claim 1 wherein one to two of R to R is a fatty acid ester group and has two to 19 carbon atoms.

3. A tobacco smoke filter according to claim 2 wherein the chain length of the polyalkylene glycol residue is l to 50 moles.

4. A tobacco smoke filter according to claim 3 wherein the compound is a sucrose or glucose derivative.

5. A tobacco smoke filter according to claim 4 wherein the polyalkylene glycol group has eight to 10 glycol units and the fatty acid ester group has two to l5 carbon atoms.

6. A tobacco smoke filter according to claim 1, wherein said filter-forming material is crimped cellulose acetate fibers.

7. A tobacco smoke filter according to claim 1 wherein said filter-forming material is polyolefin fibers.

8. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose fibers.

9. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose paper.

10. A tobacco smoke filter according to claim I wherein said filter-forming material is polyvinyl alcohol sponge.

11. A tobacco smoke filter according to claim 1 wherein said filter-forming material is a member selected from the group consisting of polystyrene sponge and polyvinyl acetate sponge.

12. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose acetate sponge.

13. A tobacco smoke filter according to claim 1 wherein said filter forming material is crimped fibers having a single fiber denier of l to 10 and a total denier of 20,000 to 100,000.

14. A tobacco smoke filter according to claim 2, wherein said crimped cellulose acetate fibers have a single fiber denier of l to 10 and a total fiber denier of 20,000 to l00,000.

l I i i 

2. A tobacco smoke filter according to claim 1 wherein one to two of R1 to R8 is a fatty acid ester group and has two to 19 carbon atoms.
 3. A tobacco smoke filter according to claim 2 wherein the chain length of the polyalkylene glycol residue is 1 to 50 moles.
 4. A tobacco smoke filter according to claim 3 wherein the compound is a sucrose or glucose derivative.
 5. A tobacco smoke filter according to claim 4 wherein the polyalkylene glycol group has eight to 10 glycol units and the fatty acid ester group has two to 15 carbon atoms.
 6. A tobacco smoke filter according to claim 1, wherein said filter-forming material is crimped cellulose acetate fibers.
 7. A tobacco smoke filter according to claim 1 wherein said filter-forming material is polyolefin fibers.
 8. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose fibers.
 9. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose paper.
 10. A tobacco smoke filter according to claim 1 wherein said filter-forming material is polyvinyl alcohol sponge.
 11. A tobacco smoke filter according to claim 1 wherein said filter-forming material is a member selected from the group consisting of polystyrene sponge and polyvinYl acetate sponge.
 12. A tobacco smoke filter according to claim 1 wherein said filter-forming material is cellulose acetate sponge.
 13. A tobacco smoke filter according to claim 1 wherein said filter forming material is crimped fibers having a single fiber denier of 1 to 10 and a total denier of 20,000 to 100,000.
 14. A tobacco smoke filter according to claim 2, wherein said crimped cellulose acetate fibers have a single fiber denier of 1 to 10 and a total fiber denier of 20,000 to 100,000. 